Gandalf: Why couldn't he connect Thrain to Thorin?

[Tinman]

I have been reading a bit into gandalf's involvement in middle earth, and have come across a subject I feel is not well explained. Gandalf located Thrain in Dol Guldur, retrieving a map and key from him, but did not know who the dwarf was, or what to do with the items once he received them. He kept them on his person until, by luck or fate, he met thorin oakenshield in bree, sparking the events that would lead to The Hobbit.

I have a few problems with this. For one, Gandalf had been actively searching for Thrain prior. Acording to FOTR:


"Good Gimli!" said Gandalf. "You encourage me. We will seek the hidden doors together. And we will come through. In the ruins of the Dwarves, a dwarf's head will be less easy to bewuilder than Elves or Men or Hobbits. Yet it will not be the first time that I have been to Moria. I sought there long for Thrain son of Thror after he was lost. I passed through, and I came out again alive!"~A Journey in the Dark

Thrain was captured in 2845... and Gandalf located Thrain (though he claims unknowingly) five years later in 2850.

I find it hard to believe that he could find a Tortured, tormented dwarf in the bowels of the Dark Lord, complete with a map of the lost kingdom of the very Dwarven king he had been searching for within the last five years, and never drawn a connections.

Certainly, if he showed the map and key to any dwarf of Blue mountains or the Iron hills... and told of the tortured prisoner, they would have told him who he had been dealing with. Even if they couldn't draw the conclusion, wouldnt they say "Well... i dont know who he is, but those items looks to be significant... maybe you should try asking thorin, the heir to that palace whose map you have (complete with instructions on a secret door that could very well help him reclaim it)... he lives over yonder."

Is it possible that gandalf is not being quite truthful? That he wanted to wait to handle smaug until he felt the time was right? Perhaps he did know it was thrain he had spoken with, and that he was just to busy to make the trip until he realized the significance of the dwarves handling smaug?

[Storm]

Is it possible that gandalf is not being quite truthful? That he wanted to wait to handle smaug until he felt the time was right? Perhaps he did know it was thrain he had spoken with, and that he was just to busy to make the trip until he realized the significance of the dwarves handling smaug?

Unfortunately I don't have anything to back this up and part of my knowledge might be blended with stuff published by ICE only, but...

I think Gandalf knew perfectly well whom he was dealing with when he found Thrain in Dol Guldur. What eludes me, and puzles me to this day is the very same question about the map and the key: how could Thrain possibly have hid these items from Sauron over all these years when he was imprisoned and tortured? Certainly he could not do so on his body. But in his holding-cell? I'm quite sure he would have been moved every now and then during these years. So, perhaps he had stashed away the items in one cell and remembered their location and Gandalf had to search the catacombs of Dol Guldur for them...?!?

The fact that Gandalf didn't go to Thorin right away is, at least for me, perfectly well "explained away" with the facts that wizards never arrive too early or too late...they always arrive when they intend to...and in fact the motivations of wizards are always obscure and not easily understood. You better not interfere or meddle with wizards affairs!
Besides that it might really be that Gandalf is a strong believer in fate and it's subtle workings in Middle-earth. Therefore he might have held the items all these years WAITING for a situation where they might present themselves useful instead of actively seeking out such an opportunity. Actually he was in fact forbidden to take an active part in helping the Free People in their efforts to stop the shadow and he might already have been stretching his options at that time.
I guess he was deliberately vague about how the items came on him because of this.

But that's just my two cents. And never forget: dwarves are easy to anger if approached the wrong way and their enmity is nothing taken lightly - even for Gandalf!!!